Pyridine → Methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylate

HRID 1799092Notes

Reaction equation

HRID 1799092 reaction equation
Cl[C:2]1[C:11]([NH:12][C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25].N1C=CC=CC=1>CC1C=CC(C)=CC=1>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]1[S:25][C:2]2[C:11]([N:12]=1)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 58551882HCID 58551882, compound

Product 1

HCID 58551887Methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 6-chloro-5-(2-nitrobenzamido)nicotinate (1 eq), P2S5 (2.1 eq), and pyridine (7.6 eq) in p-xylene was heated at 130° C. for 2 h. The clear liquid was decanted and allowed to cool to room temperature. The resultant precipitate was collected by filtration and dried to give methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylate (57% yield).

Workup

  1. customThe clear liquid was decanted
  2. temperatureto cool to room temperature
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-2aec5ce4bd534a61a681851856f038df
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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